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Methylthiomethyl ether
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<h2 id="alcohol-protection">Alcohol protection</h2> <p>Methylthiomethyl (MTM) group is used as a <a href="/facts/Protecting_group/f92hVwHl">protecting group</a> for <a href="/facts/Alcohols/Y0SCTDkh">alcohols</a> in <a href="/facts/Organic_synthesis/aprl6Iq7">organic synthesis</a>. This type of alcohol protecting group is robust under mild acidic reaction conditions. </p> <h3>Most common protection methods</h3> <ul><li>Treatment of alcohol with <a href="/facts/Sodium_hydride/Pnsh2T64">sodium hydride</a> and methylthiomethyl halide</li> <li><a href="/facts/Dimethyl_sulfoxide/T4HSYfuC">Dimethyl sulfoxide</a> (DMSO) and <a href="/facts/Acetic_acid/uyBKA2Pd">acetic acid</a> (AcOH) in <a href="/facts/Acetic_anhydride/hGxHam3M">acetic anhydride</a> (Ac2O) at ambient temperature</li></ul> <h3>Most common deprotection methods</h3> <ul><li><a href="/facts/Mercury(II)_chloride/aUAKsq6a">Mercury (II) chloride</a> (HgCl2); <a href="/facts/Calcium_carbonate/UQ1wLFna">calcium carbonate</a> (CaCO3) is used as an acid scavenger for acid sensitive substrates<a class="footnote-ref" id="fnref:1" href="#fn:1"><sup>1</sup></a></li></ul> <ul><li><a href="/facts/Methyl_iodide/uUKdue80">Iodomethane</a> (MeI) in presence of <a href="/facts/Sodium_bicarbonate/S9oSol0R">sodium bicarbonate</a> (NaHCO3) at elevated temperatures (this type of reaction is generally carried out in acetone/H2O solution)</li> <li><a href="/facts/Magnesium_iodide/snuYv4wJ">Magnesium iodide</a> (MgI2) and acetic anhydride (Ac2O) in <a href="/facts/Diethyl_ether/Ep20vEdj">ether</a> at ambient temperature<a class="footnote-ref" id="fnref:2" href="#fn:2"><sup>2</sup></a></li></ul> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>Corey, E. J.; Bock, Mark G. (1975-01-01). "Protection of primary hydroxyl groups as methylthiomethyl ethers". Tetrahedron Letters. 16 (38): 3269–3270. doi:10.1016/S0040-4039(00)91422-9. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>Wuts, Peter G. M.; Greene, Theodora W. (2006). Greene's Protective Groups in Organic Synthesis, Fourth Edition - Wuts - Wiley Online Library. doi:10.1002/0470053488. ISBN 9780470053485. <a href="9780470053485" target="_blank">9780470053485</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> </ol>